Esters-buliding-blocks

Related Products of 541-16-2, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 541-16-2 as follows.

Compound 168 (80 mg, 0.14 mmol) was dissolved in 10 mL of acetonitrile and iodomethane (86 [mu] L, 1.39 mmol) was added and reacted at room temperature for 24 hours.The reaction solution is directly concentrated,The compound 168 was rinsed with a 50 mL mixture of petroleum ether: dichloromethane = 4: 1 (v / v)Of the imidazole moiety of iodomethane salt 75 mg, yield 76%; A tryptamine (2.0 g, 12.5 mmol) was dissolved in 20 mL of tetrahydrofuran,(3.5 mL, 25 mmol) and tert-butoxycarboxylic anhydride (3.03 g, 15.0 mmol) were added in turn followed by reaction at 10 C for 1 hour,The reaction solution was poured into 100 mL of ice water and extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate, concentrated by flash column chromatography, and eluted with petroleum ether: ethyl acetate = 2: 1 (v / v) to give N- [2- (3-indole) ethyl] carbamic acid tert-butyl ester, yield 97%;A solution of tert-butyl N- [2- (3-indole) ethyl] carbamate(1.8 g, 6.92 mmol) was dissolved in 110 mL of THF / H2O (10: 1)Down to 0 C,DDQ (3.1 g, 13.8 mmol) was added and reacted at this temperature for two hours.The reaction solution was poured into 200 mL of ethyl acetate and washed with saturated sodium bicarbonate solution to a colorless color,The ethyl acetate layer was dried over anhydrous sodium sulfate and concentrated. The column was separated by flash column chromatography,Petroleum ether: ethyl acetate = 1: 1 (v / v)2- [3-oxo-2- (3-indole) ethyl] carbamate in a yield of 63%A solution of tert-butyl N- [2-oxo-2- (3-indole) ethyl] carbamate (200 mg, 0.73 mmol)Treated with 5 mL of trifluoroacetic acid, reacted at 10 C for one hour,Benzene (5 mL x 3 times) was obtained by azeotropic removal of trifluoroacetic acidN- [2-oxo-2- (3-indole) ethyl] trifluoroacetic acid in 185 mg, yield 93%.(75.0 mg, 0.105 mmol) of the imidazole moiety of compound 168 was dissolved in 2 mL of DMF and triethylamine (73.0 [mu] L, 0.525 mmol) and N- [2-oxyadienyl-2- (3-indole(85.4 mg, 0.315 mmol, 3.0 equiv) was added and reacted at room temperature for 24 hours.The reaction solution was diluted with 10 mL of ethyl acetate, washed with 1N hydrochloric acid,Dried over anhydrous sodium sulfate and concentrated.Semi-preparative HPLC separation, MeOH: H2O = 9: 1 (v / v)Eluting to give 40 mg of 3′-N- [N- (2-oxo-2- (3-indolyl) ethyl) aminothioformyl] staurosporine (169) in 56% yield.

According to the analysis of related databases, 541-16-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ocean University of China; Key Laboratory of Chemistry for Natural Products of Guizhou Province Chinese Academy of Sciences; Zhu, Weiming; Ma, Hongguang; Wang, Liping; Xu, Zhihong; Zhang, Yapeng; Wang, Yi; Liu, Peipei; (142 pag.)CN106083830; (2016); A;,
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36692-49-6, name is Methyl 3,4-diaminobenzoate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Product Details of 36692-49-6

A mixture of (4-tert-butyl-phenoxy)acetic acid (300 mg, 1.4 mmol), 3,4-diaminobenzoic acid methyl ester (300 mg, 1.4 mmol) in PPSE (4.8 mL) was heated at 160 C. for 4 h. At the end of the reaction period, the mixture was taken to ethyl acetate and neutralized with aqueous sodium bicarbonate. The organic layer was separated and the aqueous solution extracted with ethyl acetate. The combined extracts were dried over anhydrous MgSO4, filtered and the solvent was removed with rotary evaporator under reduced pressure. The residue was purified by flash chromatography (EtOAc:Hexane=1:9-4:6) to afford 2-2,4-tert-butyl-phenoxymethyl)-1H-benzoimidazole-5-carboxylic acid methyl ester as a colorless powder (547 mg, 80% yield). 1H-NMR (CDCl3, 300 MHz) 8.39 (1H, s, aromatic), 8.03 (1H, d, J=8.1 Hz, aromatic), 7.66 (1H, d, J=7.8 Hz, aromatic), 7.27 (2H, d, J=8.4 Hz, aromatic), 6.88 (2H, d, J=8.7 Hz, aromatic), 5.43 (2H, s, OCH2), 3.95 (3H, s, OCH3), 1.27 (9H, s, t-butyl), NH not detected.

The synthetic route of 36692-49-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY; US2009/306078; (2009); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 107045-28-3, name is tert-Butyl 4-(aminomethyl)benzoate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C12H17NO2

46.4 g (200 mmol) of 4-chloro-1,8-naphthalic anhydride and 41.4 g (200 mmol) of tert-butyl 4-aminomethylbenzoate were placed in 250 mL of EtOAc to form a suspension.Stir at RT for 16 hours.The resulting precipitate was filtered and dried at 50 C for 8 hours.A white powder of 48 g (yield 57%) was obtained.

According to the analysis of related databases, 107045-28-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Institute of Biophysics, Chinese Academy of Sciences; Suzhou Shoutong Science And Technology Co., Ltd.; Dai Yu; Zhao Jianyong; Zhang Wenxin; (21 pag.)CN108675989; (2018); A;,
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Application of 6933-47-7,Some common heterocyclic compound, 6933-47-7, name is Methyl 4-amino-2-methylbenzoate, molecular formula is C9H11NO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Synthesis 184-(3,5-Dichloro-4-ethoxybenzamido)-2-methylbenzoic acid (AAA-019)Step (i): Methyl 4-(3,5-dichloro-4-ethoxybenzamido)-2-methylbenzoate (3)1A solution of 3,5-dichloro-4-ethoxybenzoic acid (1) (285 mg, 1.21 mmol) and DIPEA (1.05 mL, 6.05 mmol) in DMF (2.5 mL) was added to HATU (690 mg, 1.82 mmol) and the orange mixture was stirred for 5 min prior to the addition of methyl 4-amino-2- methylbenzoate (2) (200 mg, 1.21 mmol) in DMF (1 mL). The resulting dark orange solution was stirred overnight for 18 h. 2 M HCI (10 mL) was added and stirring continued for 10 min, and then the mixture was extracted with diethyl ether. The organic layer was washed with water (3 x 15 mL), dried over MgS04, filtered and the solvent was evaporated in vacuo. The yellow residue was purified by silica gel chromatography (40 g, 0-100% EtOAc in isohexane) to afford methyl 4-(3,5-dichloro-4-ethoxybenzamido)-2- methylbenzoate (3) (267 mg, 56%): m/z 380 (M-H)” (ES”). 1H NMR (400 MHz, CDCI3) delta: 7.97 (1 H, s), 7.80 (3H, m), 7.54 (1 H, dd), 7.51 (1 H, d), 4.18 (2H, q), 3.89 (3H, s), 2.63 (3H, s), 1.49 (3H, t).

The synthetic route of 6933-47-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KING’S COLLEGE LONDON; CORCORAN, Jonathan Patrick Thomas; KALINDJIAN, Sarkis Barret; BORTHWICK, Alan David; ADAMS, David Reginald; BROWN, Jane Theresa; TADDEI, David Michel Adrien; SHIERS, Jason, John; WO2011/27106; (2011); A1;,
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Related Products of 20372-66-1, A common heterocyclic compound, 20372-66-1, name is Methyl 2,4,5-trifluorobenzoate, molecular formula is C8H5F3O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Methyl 2,4,5-trifluorobenzoate (DSL Chemicals; 950.61 mg; 5 mmol; 1 eq.), sodium cyanide (306.30 mg; 6.25 mmol; 1.25 eq.) and tetrabutylammonium bromide (2 014.82 mg; 6.25 mmol; 1.25 eq.) were dissolved in DMF (10 mL) . The resulting mixture was heated at 6O0C overnight. As the reaction was not complete, sodium cyanide (306.30 mg; 6.25 mmol; 1.25 eq.) was added and the mixture was stirred at 6O0C for additiona 24 h. The resulting dark pink solution was diluted with EtOAc and washed with brine several times. It was dried over MgSO4, filtrated and evaporated, resulting into a sticky dark red oil, which was purified by flash chromatography (Sitheta2 100 g, EtOAc / c-hex 1 :9 until 1 :1 ), affording the title product. 1H NMR (DMSO-d6, 300 MHz) delta 7.77 (dd, J = 5.45, 8.41 Hz, 1 H), 7.42 (dd, J = 4.99, 8.88 Hz, 1 H), 3.96 (s, 3H). LC/MS (Method A): 463.2 (M-H)”; 465.2 (M+H)+. HPLC (Method A) Rt 3.63 min (Purity: 99.9%).

The synthetic route of 20372-66-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SERONO S.A.; WO2009/43889; (2009); A2;,
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These common heterocyclic compound, 66315-16-0, name is Methyl 3-amino-4-(methylamino)benzoate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. category: esters-buliding-blocks

DCC (12.3 g, 59.7 MMOL) was added to an ice-water cooled solution of N-BOC 8-alanine (10.0 g, 52.8 MMOL) and methyl 3-amino-4-methylaminobenzoate (8.27 g, 45.9 MMOL) in CH2CI2 (400 mL). The reaction mixture was stirred 1 h at 0C and overnight at room temperature, then the insoluble urea was removed by filtration. After concentration, the residue was dissolved in ethyl acetate and washed with 5% NAHCO3, followed with saturated NaCl. The organic solution was dried over NA2SO4, concentrated, and purified by chromatography over silica gel eluted with 1: 2 hexane-EtOAc to afford 15.02 g (93%) of desired product as a white SOLID. 1H NMR (300 MHz, D6-DMSO) o 9.06 (s, 1H), 7.70 (d, J=1.8 Hz, 1 H), 7.66 (dd, J=8.4 Hz, J=1.8 Hz, 1 H), 6.87 (s, 1 H), 6.59 (d, J=8.4 Hz, 1 H), 5.89 (d, J=4.8 Hz, 1 H), 3.74 (s, 3H), 3.23 (q, J=6.9 Hz, 2H), 2.76 (d, J=4.8 Hz, 3H), 2.46 (t, J=6.9 Hz, 2H), 1.38 (s, 9H). Anal. Calc’d. FORC17H25N305 : C, 58.11 ; H, 7.17 ; N, 11.96. Found: C, 58.28 ; H, 7.09 ; N, 11.92.

The synthetic route of Methyl 3-amino-4-(methylamino)benzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMACIA CORPORATION; WO2004/99131; (2004); A2;,
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Reference of 6962-92-1, These common heterocyclic compound, 6962-92-1, name is 4-Chlorobutyl acetate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Preparation 6 To an ice-cooled solution of 3-(3-oxo-2,3-dihydropyridazin-6-yl)-2-phenylpyrazolo[1,5-a]pyridine (2.0 g) in N,N-dimethylformamide (20 ml) was added portionwise sodium hydride (60% dispersion in mineral oil; 0.31 g). After addition was finished, the mixture was stirred for 15 minutes in an ice-bath. To this mixture was added 4-chlorobutyl acetate (1.1 g), and the reaction mixture was stirred for 24 hours at room temperature, and then for 36 hours at 70 C. After being cooled to room temperature, the reaction mixture was concentrated. The residue was partitioned between ethyl acetate and water. The organic layer was separated and the aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed with water and sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and concentrated. Purification of the residue by column chromatography on silica gel (using 3:1 mixture of chloroform and ethyl acetate as eluent) gave 3-[2-(4-acetoxybutyl)-3-oxo-2,3-dihydropyridazin-6-yl]-2-phenylpyrazolo[1,5-a]pyridine (2.6 g). An analytical sample was prepared by recrystallization from diisopropyl ether. mp: 102-103 C. IR (Nujol): 1720, 1660 cm-1 NMR (CDCl3, delta): 1.7-1.9 (2H, m), 1.9-2.2 (2H, m), 2.05 (3H, s), 4.16 (2H, t-like, J=ca. 6Hz), 4.31 (2H, t-like, J=ca. 6Hz), 6.77 (1H, d, J=10Hz), 6.8-7.0 (1H, m), 7.02 (1H, d, J=10Hz), 7.2-7.4 (1H, m), 7.4-7.5 (3H, m), 7.6-7.7 (2H, m), 7.9-8.0 (1H, m), 8.5-8.6 (1H, m) MASS m/z: 402, 343, 287 Anal. Calcd. for C23 H22 N4 O3: C 68.64, H 5.51, N 13.92 (%) Found: C 68.31, H 5.48, N 13.76 (%)

The synthetic route of 6962-92-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fujisawa Pharmaceutical Co., Ltd.; US5338743; (1994); A;,
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Related Products of 653-92-9, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 653-92-9 as follows.

(b) Methyl 2-cyano-4-fluorobenzoate; Methyl 2-bromo-4-fluorobenzoate (1.0 g, 4.29 mmol; see step (a) above) was dissolved in dry DMF (5 mL) and degassed with N2-gas for 5 minutes. CuCN (769 mg, 8.58 mmol) was added and mixture was degassed again before the temperature was raised. The reaction mixture was refluxed for 75 minutes. NaCN (aq, 10%) was added and the mixture was extracted with DCM. The DCM phase was dried through a phase separator and the solvent was removed in vacuo. The crude product was dissolved in toluene and washed once with water. The organic phase was dried over MgS04 and filtered. The solvent was removed in vacuo to give the product (in 94% yield), which was used without further purification. ‘H NMR (500 MHz, CDC13) 5 4.01 (s, 3H), 7.35-7. 42 (m, 1H), 7.52 (dd, 1H), 8.15-8. 23 (m, 1H)

According to the analysis of related databases, 653-92-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; WO2005/58826; (2005); A1;,
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Synthetic Route of 3469-00-9,Some common heterocyclic compound, 3469-00-9, name is Methyl Diphenylacetate, molecular formula is C15H14O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of diisopropylamine (0.17 mL, 1.19 mmol) in THF (1 mL) was added n-BuLi (2.5 M in hexane, 0.4 mL, 0.994 mmol) at -78 C. The reaction mixture was stirred at this temperature for 30 min, followed by stirring at -5 C for 30 min. Then, the reaction mixture was cooled to -78 C and diphenyl methylacetate (S6) (0.15 g, 0.66 mmol) in THF (2 mL) was added. After stirring at -78 C for 15 min, (E)-4,6-iodoheptadiene (S11) (0.16 g, 0.72 mmol) was added. The resulting solution was stirred at rt overnight. The reaction mixture was quenched with satd aq NH4Cl (10 mL) and extracted with EtOAc (2 x 50 mL). The extract was washed with water and brine, dried (MgSO4), filtered, and concentrated by rotary evaporation. Column chromatography of the residue (20:1 hexane/EtOAc) gave S12 (120 mg, 63%) as colorless oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl Diphenylacetate, its application will become more common.

Reference:
Article; Chandrasekhar; Ryu, Jae-Sang; Tetrahedron; vol. 68; 24; (2012); p. 4805 – 4812;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 4630-80-2 as follows. Formula: C7H12O2

General procedure: A solution of 1.02 mL (19.49 mmol) of acetonitrile in 13 mL of THF was cooled to 0 C and added 11.4 mL (19.49 mmol) of potassiumt-pentoxide solution (1.7 M in toluene) dropwise with constant stirring. The reaction mixture was stirred at room temperature for 2h. Reaction mixture was cooled again to 0 C and 1.32 g (9.74 mmol) of methyl benzoate was added dropwise followed by stirring for additional 2h at room temperature. After completion of the reaction (by TLC), crude mixture was quenched with 1NHCland extracted with ethyl acetate. The organic layer was washed with brine and dried over MgSO4. The crude was purified with column chromatography using hexane and ethyl acetate eluent to yield 0.56 g (40%) 3-oxo-3-phenylpropanenitrile.

According to the analysis of related databases, 4630-80-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Rana, Sandeep; Sonawane, Yogesh A.; Taylor, Margaret A.; Kizhake, Smitha; Zahid, Muhammad; Natarajan, Amarnath; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3736 – 3740;,
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